Showing Myself

Ok, here is what happened on my next trip to Chicago. Sorry that it isn't wall to wall sex!

Anyway, the next morning I really wanted Kari to take some pics of me so I could show Jim, but it didn't work out. Grrrrr! But I finally made it up to Chicago

In addition to him being incredibly sexy and smart and funny, Jim is very kind. Oh, I wish I could turn myself back 20 years and meet someone like him! Nonetheless, we finally were in Chicago again at the same time. He had arrived a day earlier, and I arrived in the morning and had to go straight to work. God, the day dragged on! Finally, I got to the hotel and cleaned up and dressed in a sexy white cotton dress with a very sheer bra and panties underneath. They were light grey with a black outline and I knew Jim would be impressed! If you haven't noticed by now, I am very feminine and always dress up when I go out in public.

I texted him, and we agreed to meet in the lobby in 30 minutes. Finally the moment arrived and I came down and saw him sitting in the lobby as handsome as ever. I didn't want to make him self-conscious about being with an older woman, so I just gave him a warm hug at first, and whispered that I was practically naked underneath.

But then I asked him if he would mind taking me to Macy's quickly to pick up some nylons, and that it was no more than a mile away. Of course he said it wasn't a problem, and then we would come back and have dinner. It was raining terribly, but ever the gentleman, he had an umbrella ready and waiting.

I told him to just drop me off at one of the entrances, and I wouldn't be more than five minutes. I went in, quickly bought the nylons, and then went out another entrance. I texted Jim and said I didn't see him, and that I must have gotten turned around. So I dashed through the parking lot in the pouring rain around to the entrance he was at, and jumped in his car, drenched.

He looked at me like I was crazy, and said, "Jennifer, why did you do that?? You know I would have driven around and picked you up!"

"Well, you know what happens to a woman dressed like me in the pouring rain? They look practically naked. Guess I have to go back to the hotel and change."

"Wait, you did that on purpose?"

"Jim, you know how it excites me to be looked at, and Americans are soooooo stuffy about nudity, so I thought I could get away with this. What can they say? A lady gets caught in the rain wearing a clingy summer dress and now she has to dash back to her room and put on something dry. I'm the victim here, and they shouldn't be staring anyway, right?"

Jim shook his head and said, "You are unbelievable."

We made the short trip back to the hotel, but I told him to park towards the back and leave the umbrella in the car, because for this to look believable he would have to be at least a little bit wet too.

Jim sighed, and said, "I know if I argue, you'll just come up with something even more outrageous, so ok."

We got out of the car and raced to the hotel lobby, and luckily there were quite a few people milling about either checking in or waiting for the little happy hour bar to open. I looked down at myself, and my nipples were clearly visible through the dress, as was the outline of my panties. The dress was adhered to my legs as I walked through the lobby and people turned around and looked. I made a show of it.

"Oh, I know, I told him we needed an umbrella but Mr Smart Guy here said it would be no problem, he'd just drop me off at the entrance at the mall and come back when I'm ready. I guess he didn't make it clear which entrance! Come on Jim, I'm soaking wet!"

Jim looked at them and just held p his hands and said, "I'm at fault. I didn't see this coming."

It was such a hot feeling. The men didn't want to take advantage of my misfortune, but they couldn't take their eyes off me. My wet dress left very little to the imagination! We got to the elevator, and luckily we had to wait with several other people, and the guys were making sideways glances at me. The door popped open, and several people stepped out and saw me, and I said, "Sorry, got caught in the rain! I couldn't have picked a worse outfit!" We got in the elevator with several guys, and we finally stepped out on our floor, knowing that no one was going to use the "close" button to make it go up sooner.

I pulled him into my room and handed him my phone and said "Take some pictures of me like this, I want to know exactly what they saw. I am so wet, and not just from the rain."

I did some poses from the front and back, sat in the chair with my legs parted and so the dress pressed against my pussy, and I even stood in front of the AC blower so it would make my nipples hard for a better shot.

"Jim, that was so invigorating! You have no idea how that felt! Come here."

We stripped off our clothes and made mad love. I told him we could take our time later, but right then I wanted him so bad and to take me any way he wanted, and then I wanted to feel his cum all over my chest.

He laid down and pulled me on down top of him, and put his strong hands on my hips and guided me down on his cock. He moved his body upwards as I slid down, and I don't think I had ever felt him so deep before. Neither of us would last long like this.

"God Jim, it really seems like you missed me. I wanted to pull my wet dress off in the elevator in front of everyone! That made me so hot!"

"You didn't need to. You were practically naked anyway."

"Just hearing you say that just turns me on Jim. I'm squeezing myself around your cock. Do you feel it?"

I got my answer when he started thrusting even more intensely. Because of the way I used to play years ago in the theaters, I was used to teasing myself and delaying my orgasm for a long time, but now I just wanted to cum.

"Jim, I'm right there, but don't cum yet. I want you to soak me. I want to see your cum pour out of your cock."

I grabbed his shoulders and let myself go. I could barely control myself as I convulsed on his cock! We definitely were going to have an amazing week!

After he made me cum, I got on my back and told him to straddle my chest so I could suck his cock. He entered my mouth and I stroked him with my hand, wanting to make him cum so hard. I brought him to the edge and then stopped, over and over. He said he was going to cum no matter what, so I let him slide out of my mouth and I stroked him until he covered me! He collapsed beside me as I looked at his cum, as though it was the first time we'd been together.

I jumped up after a minute and got my bag, saying I had to pick out some dry things.

"Oh, ok, I do too, so I'll meet you in the lobby at 8:30?"

I called from the bathroom, "Perfect Jim, see you then!"

I met him in the lobby once again, wearing a leather skirt and blouse with a camisole underneath. There were still a few familiar faces down there from earlier, and I just shrugged and said, "I guess I'm better prepared for the rain this time. Sorry about that earlier!"

We sat at the bar and told the bartender we'd have a drink first and then get a table. I asked Jim if he liked our little adventure.

"Well, it really paid off for me I guess."

"It paid off for me too. I'm still wet thinking about it."

I took out my lip balm, and touched up my lips.

"It's my favorite kind. Want some? I need it during this summer heat up here."

"No, I'm fine, what kind is it?"

"Oh, it's your cum."

Jim practically choked on his drink and said, "What??"

"Jim, you know I really adore you, but are you paying any attention at all? You have shot your cum in my mouth, on my panties, on my face, everywhere, right? And how many times did I jump up and clean it off? Never. So what did you think I was doing earlier when I jumped up? I was putting it in my little lip balm container. You sure you don't want some?"

"The only thing I'm sure about is that I'm bringing my own toothpaste If I ever stay at your place."

I laughed and said, "Oh Jim, I wish you could really know how much I'm attracted to you. I love your humor and your kindness and understanding, and your incredible lovemaking. And you let me be me without thinking I'm an embarrassment to you."

"No, Jennifer, you aren't an embarrassment. And yes, we have really seemed to hit it off. And I know you're concerned about the age difference, but let's not think about that. You aren't a booty call to me at all."

"Thank you Jim, I appreciate that, really, and I'll try to behave for at least two hours, ok?"

"I don't think that's possible. It's only been two hours since we met in the lobby earlier, and look what you've already done. We're sitting at the hotel bar with my cum on your lips."

"Well, I'll still try. Now, I need you to come out of your shell. What are your deepest fantasies and desires? Don't hold back, there are no rules as long as it's consensual. I have a whole diary from my earlier days, and maybe I'll let your read it sometime. All I ask is that you never hurt me or humiliate me, because I trust you completely."

"Don't ever worry about that. I won't, not to mention your revenge would make even Hitchcock's skin crawl."

"Ok, don't ignore the question, tell me a fantasy."

"I don't know, it's embarrassing to say them, that's why they're called fantasies."

"See, that's what I mean! Let yourself go Jim! Should I start asking random people what their fantasies are? Because you know I will, unless you tell me one of yours."

"I'll bet they say it's to see a woman with a see-through dress and sheer bra get caught in the rain."

"I love that Jim, you are so clever. But you had your chance." I saw two young ladies about Jim's age walking towards us, and decided to bring them into our little discussion. They were both attractive, and one was married. The single one was very cute, with a tall, slender figure. Before Jim realized it, I spoke up and said, "Excuse me, I need your opinion on something?"

Jim had that Jim look, afraid of what might come out of my mouth, but he knew it was too late.

The two girls looked at me, and I said, "So, I'm Jennifer and this is my friend Jim, and I'm going to tell you he is one of the smartest and kindest men I've ever known. And no, I'm not trying to fix him up with one of you, and he isn't my guy and he isn't trying to pick me or anyone else up. But he's kind of shy, and I just want him to be more comfortable talking."

Jim looked at them and said, "I'm really not shy. I have no idea what she's talking about."

"Right Jim. You just told me it's embarrassing to tell someone a fantasy. Listen, he and I were joking around and I shared a fantasy of mine, and he said he didn't have any. That's impossible. So I'll tell you what mine is and then you tell me if I'm weird or disgusting."

Jim just muttered, "Oh my God...."

"Ok, in college there was this really hot professor, and I had a fantasy that after class one day I would go up and flirt with him and tease him, and then we would start making out until, you know, we had sex. It's just a fantasy that I found exciting. It's ok, right?"

The girls nodded, and agreed that they've both had fantasies about college professors too.

Jim jumped in and said, "Yeah, but if I had said my fantasy is to be a college professor and then one of my students came up and flirted with me and then we had sex, you would have called me a perv."

"Oh Jim, you don't get it. Yes, that would be a pervy fantasy because you are the one in power. In our fantasy, we're students but we take power from him. It's so exciting!"

The girls agreed completely and I asked them what they had for a fantasy. The married one said, "Well, the other day I was upstairs and I looked out the window and there was a guy across the street trimming trees and I realized he could look right in my window if he wanted to. I imagined how hot it would be if I had just gotten out of the shower and had no idea he was there, and got on the bed and did some work on my laptop and didn't even notice him."

I turned to Jim and said, "See, that is really hot! I would love that to happen to me! But Jim, remember your fantasy can't be the guy trimming trees, because no one likes a peeping tom. That's how women and men differ. So, your turn now. Just try."

Jim thought for a moment, and then said, "Ok, I'm working at a hotel in housekeeping, and one evening a guest requests extra towels. I walk in and say, 'Housekeeping, you needed extra towels?', but the guest is laying on the bed naked. It was a total setup, and she pretends to be shocked and then tells me to come over and join her."

The three us just looked at Jim, and then the married girl said, "Not bad, maybe I should leave my room key", and laughed. I said, "I don't know Jim, that sounds too contrived, like someone else thought of it", and I glared it him. I looked at the other woman, and asked her what her fantasy was. I also looked at her more closely, and noticed she was very attractive. She was very pretty, feminine, and quiet. She was the observant type too, whereas her friend did the talking.

"Oh, I don't know, whatever happens I guess."

With anyone else I would have pushed her a little bit, but not her. She had a very kind and sincere demeanor, but was also the type who didn't need the attention.

"That's fine, it's always the quiet ones anyway that are the wildest", and I smiled at her.

We chatted for a few more minutes, and I got the sense that the quiet girl liked Jim. So, I said, "You know, we're going to have a bite to eat, and I assume you are too, so afterwards lets have a glass of wine and chat some more. I'm sure Jim would doesn't mind spending his evening with two beautiful ladies like yourselves."

They agreed, and I knew the quiet girl couldn't wait. I said to Jim, "The quiet one is really into you. I sense it. And she's your age. You need to talk to her."

"I'm here with you, not to meet someone else. There is no interest whatsoever. Besides, she could be from anywhere."

"Jim, a woman sees these things. But ok, it still won't hurt to have a glass of wine."

We had dinner at the bar, and during the dinner I got a text from Kari. I hoped nothing was wrong on their very first night alone! But I read it and was pleasantly surprised.

"Jenn, I feel silly asking you this, but I was wondering if you could suggest something I could do with Mike that would surprise him. You know what I mean?"

"Oh, feeling a little adventurous are we?"

"Well, you are so wild! I just want to surprise him."

I said to Jim, "This is so cute. I'm letting the young couple I told you about stay at my place while I'm up here, and she's asking me for sex tips to surprise him. Got any ideas?

"I'm sure you'll come up with something."

"God, I have to do everything! Ok, whatever."

I quickly texted Kari back. "Ok, get on top of him and ride him. You know how to do that, right? But before either of you cum, get off and slide down and take his cock in your mouth and tell him how you love to taste yourself all over his cock. Then hop back on. He'll be impressed, trust me."

I showed the text to Jim and asked if that was ok, and he said sarcastically that I had to include more detail.

I sent it, and I got a text back, "Ok, I'll try. How do you even casually type something like that? I'd be so embarrassed!'

"Kari, just let go and have fun. He won't judge. I'm right here if you have other questions."

Wow, now I had the visual of what Kari was doing while sitting here with Jim! I could just imagine her body as she took Mike's cock. He's in for such a treat.

"Jim, just imagine this. There is a cute young lady that looks kind of like me 30 years ago having sex in my house right now. That's going to be us later."

Anyway, we finished our dinner and then moved to the comfy chairs by the fireplace, and I motioned to the two girls to come over when they were finished.

They came over and we chatted some more, and then I said, "Jim, I don't really know you. Give us your life story in 60 seconds."

"I really don't like to talk about myself."

"Oh, there's a shocker. Just try."

Jim sighed, and said, "Well, I joined the Marines after high school, got married a year later to my high school sweetheart, did several tours overseas. During the last one my wife said she didn't know me anymore, which is code that she found someone else, and we got divorced. I didn't reenlist, and went to school instead. I studied project management, and I'm now a project manager for an architectural firm, and hate every minute of my job. I'll leave at the end of the year and get a job for a construction company that leans towards more boots on the ground. In my private life, I rarely go out. I come home and cook dinner and sit on the front steps and eat and watch the world go by. I like to read, and usually spend my evenings doing that unless there is a ballgame on. How was that?"

The married girl said, "57 seconds, very good!"

He sipped his wine and said, "Just like a good Marine."

I never knew that side of Jim. It seemed sad in a way, but he is so darned grounded and mature! It made him ten times hotter than before, if that is even possible!

I asked the quiet girl, who had since introduced herself as Lisa, about her life, and she had a similar story. She got married early, went to school, and had a couple of kids, but then the marriage fell apart. She lives in Minneapolis and has a good job, and will just continue working until her kids are settled before she even considers dating again. But then she and Jim started bantering back and forth, and they seemed to have so much in common, right down to the books they read!

I said to the married girl, "Come over to the bar with me and suggest a wine that you two like. It's on me."

We stepped over to the bar and I said, "Is it me, or do Jim and Lisa seem to have a connection? Don't they seem like they would be a good fit?"

"Oh yeah, I see it too. She never talks to guys, ever. I work with her, and she never goes out after work or anything. I had to beg her to come down here tonight, and she only came so I wouldn't be alone."

"Do me a favor. I want to get Lisa alone for a couple of minutes. Can you come up with a reason to get Jim out of here?"

"I don't know, I'll try to think of something."

We went back to the table and continued talking and laughing, and then the married girl said, "Jim, you know what? We are flying out tomorrow and I have to return my rental car in the morning, and I didn't even check where the little handle is for opening the gas cap door. Could you go out with me quickly and make sure I don't look like a fool at the gas station? Don't judge me, it happened before."

I thought to myself, "This girl is a genius!", and Jim, being the perfect gentleman, was glad to help and didn't make fun of her.

As soon as they left, I said, "You and Jim are really hitting it off. You like him? Just tell me, don't you think he's hot and super nice at the same time? I know I do."

"Oh, every guy can put on a show in the beginning. But yes, he's very nice."

Wow, that was cynical! She's been hurt before. I'll have to reassure her.

"But do you think he's handsome? I know he's attracted to you, and he is so darn picky! He never talks to women! I see his body language, the way he cocks his head to the side slightly so he doesn't miss a word. He's taking you very seriously."

"Yes, he's very handsome. It's been a fun night, thank you for inviting us."

God, she is just too sweet! Perfect for Jim!

They came back, and the married girl said she felt so stupid, because the little door just opened on its own, and she didn't even need a Marine after all.

We talked for a while longer, and I even told them of the earlier escapade of me getting caught in the rain and how Jim even pretended it was his fault just to make me feel better in front of everyone. That really scored some brownie points with Lisa. Then, we had to say our goodbyes. Jim of course just shook Lisa's hand and said it was a pleasure to meet her, blah, blah, blah, and Lisa, being old fashioned, just said she enjoyed it too and still didn't ask for his number! They left the lounge area and were walking towards the elevator, and I grabbed Jim by the shirt and yanked him close to me.